You know it's time to leave a business you built when it no longer fits the life you want — even if it's successful and you're the owner. For Sean O'Rourke, the signal was how he reacted to his alarm clock every morning: the work had become an always-on grind that no longer matched his goals. Leaving doesn't have to mean retiring or cutting ties; he stepped out of the day-to-day while staying connected to the field. The deciding factor is honesty about what you actually want, not what looks responsible from the outside.
Ellen Williams reconnects with Sean O'Rourke, a cyber liability consultant who spent twenty-five years in IT — including twelve running a firm he co-founded — for a conversation about knowing when to walk away from something you own. Sean's pause, as he puts it, is still in effect: he told his partners he was done with the day-to-day grind of technology, then rebuilt his working life around a more sustainable role. His story is about leaving well, and about being honest with yourself about what you really want.
Knowing When to Leave — Even When You're the Owner
Sean loved being one of the bosses and loved his partners and employees. But after about twenty years in technology, the work had become a millisecond-by-millisecond, seven-day-a-week business — always on call for the next crisis, from a downed connection to a ransomware demand paid in Bitcoin.
"I could see how I was reacting to the alarm clock every day, and it just was no longer something that I knew I wanted to do."
The business was healthy and he was proud of what they'd built over twelve years. That wasn't the question. The question was whether the daily reality still fit the life and the age he was moving into — and it didn't. He had the self-awareness to admit it, and the confidence that his experience would carry him somewhere new.
How do you know when it's time to leave a business you built?
You know it's time when the day-to-day no longer fits the life you want — and you can feel it before you can justify it. For Sean O'Rourke, the tell was his reaction to the alarm clock each morning after twenty years in technology that had become an always-on, seven-day-a-week grind. The business was successful and he loved his partners, but he could see where it was heading and knew it wasn't where he wanted to go. When competence keeps you somewhere your gut has already left, that gap is the signal.
You Can Step Back Without Fully Stepping Away
Sean is careful to say his pause is "still in effect" — and that it was never retirement. He didn't sever his connection to technology; he changed his relationship to it.
"At the end of the day, taking care of one company's IT is far different than taking care of a hundred different clients."
He moved into business development for an insurance brokerage, specializing in cyber insurance — a niche where his technical background makes him, in his words, a unicorn. He took it as an iterative step rather than a clean break, and the arrangement came full circle: his firm now uses his old IT company as its outsourced provider, keeping him in touch with the field. He even took on the CFO role, because he enjoys the business side others avoid.
How do you step away from a company you founded without retiring?
Leaving doesn't have to be all-or-nothing. Sean O'Rourke says his pause is "still in effect" — he exited the day-to-day of his IT firm but stayed connected to technology through a new role in cyber insurance, where his background makes him, in his words, a unicorn. He transitioned through an iterative step rather than a clean break, even using his former company as an outsourced provider. The key is to redirect your expertise into something with a saner rhythm — keeping what energizes you and shedding what drained you.
Be Honest With Your Reflection
When Ellen asked how leaders can tell it's time to pause, Sean offered the same advice he gives the students and new entrepreneurs he mentors.
"The easiest person to lie to is that reflection in the mirror."
He realized early that he'd make "a great worker but a terrible employee," so he built his life around being his own boss, where outcomes depended on his own decisions. He contrasts himself with his brother, who values toys and experiences and chose banking for the money — headaches included. Neither path is wrong, Sean says. The mistake is pretending you want something you don't. Once you can name honestly what motivates you, every other decision gets dramatically easier.
How do you figure out the right career path for you?
Be honest with your reflection — the easiest person to lie to, Sean O'Rourke says, is the one in the mirror. He realized he'd make "a great worker but a terrible employee," so he built everything around being his own boss. He contrasts himself with his brother, who values toys and experiences and chose banking for the money, headaches included. Neither path is wrong; the mistake is pretending you want something you don't. Once you can name honestly what motivates you, every other career decision gets dramatically easier.
The One Thing
Leaving something you built isn't failure — sometimes it's the most honest thing you can do. Sean O'Rourke walked away from a company he was proud of because he could feel it no longer fit his life, and he trusted that his skills would carry him somewhere that did. His one rule for every big decision: be honest with the reflection in the mirror, because it's the easiest person to lie to.
